So if you have read thru my previous blog post you have the basis of my entry into my cuckold life. I would like to say that after my college experience with Jessica and having been so properly indoctrinated into the world of Cuckoldry that I would just chalk it up to college experimentation and went on to date and have relationships that were more along the lines of the social norm however that is just not how life goes I guess. After Jessica and I went our separate ways after college I was left feeling rather unsure of myself, dating, and women in general. Were all women secretly like this, or most, was this some deep dark desire that women have but rarely live out? these questions plagued my thoughts and mind for quite a while.
I made attempts to date women and not approach the topic of previous relationships or kinks as I being a young man was unsure of how would that be received. How would they react? Would they judge, call me a homo, or freak out and think I was some weird freak? Needless to say I obviously did not have too many successful relationships immediately after having left college and the life I had. I allowed too many questions to consume my thoughts, fears, and insecurity. I went out on a great deal of first and second dates but not much further than that for years. As the years passed I became rather complacent with being single. I began to feel that being single, alone, and unattached was just how my life was heading. Mind you I grew up thinking and wanting so badly to someday find my one true love and get married, having kids and all that jazz. I so greatly dreamed of this often. Just wishing to one day be half the husband and father my father is. Needless to say here I am just having turned 40 earlier this year and I am single never married and no children. I have plenty of nephews and maybe that is just the way things were meant to be for me.
It was probably about 11 years ago I met a girl that still to this day I have the utmost weakness for. As with my previous blog post lets just say for discretion sake her name is Kate. Kate and I met at a dog park of all places. I instantly was blown away by not just her appearance but the general glow of her personality. Let me preface this by saying I am a huge fan of Rachel McAdams everything about her and the characters she plays. Kate as it would be looks amazingly like Rachel McAdams which never dawned on me at first. So Kate and I hit it off splendidly. We talked and spent a lot of time hanging out there at the park and had moved on to hanging out some outside of taking our dogs to the dog park. As luck would have it tho, Kate had a boyfriend so things kind of just fizzled out. Kate and I loosely kept in touch over time and about 5 yrs later we really got back in to communicating more and eventually began to see one another more. Kate unbeknownst to me had some issues going on that I didn't realize. She had a bit of an addiction issue and was not the most reliable person or kind of flakey I guess. I took the flakey behavior and inability to be reliable as a sign of disinterest and we kind of just fizzled out yet again. I did not know then of her addiction issue and did not find out until 6-7 months after when she apologetically came to me confessing of it and that it was a problem she has and didn't want me to think less of her or to think she didn't care about me.
So it was about 2 yrs later that Kate and I really hit things good and rolling. We were dating and things got serious. As you know from the previous post I have a kind of size issue so with that bit of concern I felt that things with Kate were in a place that because of how long we had known one another and how great of a connection we had that I could open up and speak candidly with her without worry. The talk happened to which Kate seemed to be unphased but the size issue and queried as to why I felt it would be an issue. This now led to opening up about Jessica and college. While hearing all this I could see that Kate was not only intrigued by it all she seemed to rather enjoy the aspects of it all. She began asking more pointed questions as to if I still had interest in all that and if I felt that is was a part of who I am or if I had actually enjoyed it all. I am sure it is quite obvious where this was heading. Kate with somewhat excitement as to hearing my answers asked if this was something I wanted for us. To which my answer was I am not sure cause it had been years and not really sure. I could see the excitement dwindle in her with that response. So knowing that it was something I had previously enjoyed and how much I absolutely adored Kate I said sure lets do this. To which Kate jumped up with excitement and stopped and said "wait tho. If this will not make you happy and this is not something you will enjoy I don't wanna do this" she said "I want to make you happy and hearing you talk about it I could see you get aroused and I could see that it was something you like" she followed up with. I said it was all good and lets run with it. Things went great Kate had a guy that was a previous FWB and that she felt comfortable with so she used him at first and would take pics and vids of it all and it was amazing. Things with him never progressed to my being there cause she didn't think he would take to it and might be put off by some of all she knew I had done previously. Kate's fwb began to catch feelings to which she swiftly terminated any interactions with him. Which took us into a slow down point in the cuckolding. Kate was rather new to it all so it was rather cute and funny to hear her try and be dominant and to say things to be mean or humiliate my size as it was not something she had done before but she did pick it up and get better as if it came naturally to her over time. Ket came home one day and telling me how this black guy was hitting on her at work and that he had given her his number. I told her well did you call or text him? Kate had said she hadn't and that she had never been with a black guy and was a little unsure of it. I had told Kate go for it. It's totally hot. Kate after having seen the guy at work a few more times and after some more interactions with him finally took the step and it was amazing to say the least. Unfortunately it was not long after that, that things with Kate went south again. I don't believe it had anything to do with the guy but more so I had been failing to notice Kate was struggling a bit more with her addiction issues but was masking it all very well. Kate had gotten herself into some trouble and we never got really enjoy things with the new guy after her first few times with him. She was now going into a clinic and having to get clean. I felt as tho I failed her by not picking up on the signs or little cues. She had told me she conquered it all. I foolishly believed it and blindly went along with it. After Kate's completion of the program and being released we kind of lost that spark we had. Kate and I are not really communicating much as she has a full desire to focus on getting herself in to a better place and be a better person the kind of person she once was and wants no distractions. I cannot fault her for her desire and wish to be the better side of herself. I still miss her and wish we could be together but her happiness means more. However, thru this second experience I had finally accepted the true fact of being a cuckold and of my cuckold life. To the extent I had asked and communicated with 2 girls I dated short term and asked some questions and about some of this and to which they both said yeah they knew there was something about me they saw but of course at that time didn't know anything about cuckoldry and now afterwards say a lot of things made sense now.
Will Kate and I ever rekindle and reconnect on that level again is a question I do know the answer to or if it will ever be a possibility for her. I do know this tho. I have accepted and come to terms with who and what I am. Who knows what the future holds or if I will find that one true love. But I am not as worried about trying to find love anymore these days I just will let life happen and let those come in to it that want to be in it. Now to think of what other topics to tackle in blog posts lol. Feel free to as any questions you'd like I am more than willing to respond. One thing is I do not have any personal photos on here as well I kind of live in a small super conservative town so anonymity with all this info is rather important. If you are curious why not show pis of just how much of a size issue I really have lol well, who would really want to see that lol. I mean who out there really enjoys D pics. lol Well farewell for now until I think of something else to write about or I have comments/questions to respond to.